Relax in Style: Upgrade Your Weekend Look

Wear a Pinwale Corduroy Sports Jacket

There are certain things our dads wore better than anyone. Corduroy isn't one of them. But these softer, lighter versions don't bring to mind key parties or shag carpeting. You can go from errand to gallery to dinner in this jacket and never feel stodgy or underdressed.

A lot of guys see all-white sneakers and they think Jerry Seinfeld. Doesn’t have to be that way. Try old-school lace-ups with a pair of gray flannel pants—it’s a way to dress up the kicks while dressing down the pants.

Cable-knit sweaters provide enough heft to be worn on their own, even as daylight starts dwindling. Camel hues look good with any skin tone and will set you apart from those who think winter must mean black.

Turtleneck, $985, by Gilded Age.

Photo: Peggy Sirota

Get a Pair of Slim Khakis

If you’ve resisted khakis because they’re too yellow/pleated/high-waisted, here’s a reason to reconsider. Cement-toned slim-fit khakis are the perfect pants to add to your weekend routine of all-jeans-all-the-time. And like denim, they don’t require ironing and can be worn with just about anything.

Named for the great tennis and badminton player of the '30s. Slip them on sockless and you'll never go wrong.

Photo: Tom Schierlitz

Army web belt

Issued to soldiers before World War I, now chosen by stylish guys in the know. A wardrobe staple for under ten bucks at any number of army-navy stores.

Photo: Tom Schierlitz

Blue blazer

First sported by sailors in the mid-1800s. Replace the gold buttons with dark plastic ones for a more modern look.

Photo: Tom Schierlitz

Ray-Ban Wayfarers

Introduced in the '50s and immortalized in Risky Business when Cruise decided every young pimp should own a pair.

Photo: Tom Schierlitz

Gray Russell athletic hoodie

Russell Athletic created its first sweatshirt some eighty years ago. It has never looked better.

Photo: Tom Schierlitz

Hamilton watches

Since 1893, one of the great American watchmakers. Stylish and affordable.

Photo: Tom Schierlitz

Filson jacket

Made of 100 percent virgin wool, the Filson jacket hasn't changed in design since 1914.

Photo: Tom Schierlitz

Timberland boots

A favorite of contractors, hikers, and MCs since 1973.

Photo: Tom Schierlitz

Pendleton Shetland Sweater

A dyed-in-the-wool classic from Oregon's finest maker of outdoor gear.

Photo: Tom Schierlitz

Levi's Selvage Jeans

Woven so tightly you'll think they're made of kryptonite, these high-grade 501 jeans (identifiable by the interior red trim) have been the choice of American tough guys for the better part of a century. Think Brando, Dean, Ponyboy.

There are certain things our dads wore better than anyone. Corduroy isn't one of them. But these softer, lighter versions don't bring to mind key parties or shag carpeting. You can go from errand to gallery to dinner in this jacket and never feel stodgy or underdressed.